Vacation rentals in Chesapeake

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Top-rated vacation rentals in Chesapeake

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Guest favorite

The exterior of the house is highlighted by a charming gabled roof and white clapboard siding. A stone chimney rises from the roof, and the entrance features a set of steps leading to a welcoming front door framed by large windows on either side, surrounded by lush green grass and trees.

Home in Charleston

4.89 out of 5 average rating, 311 reviews

Historic Farmhouse by Nature Preserve

We welcome you to The Little House, sensitively restored and superbly furnished. Enjoy entire house and its 2.7 acres, adjacent to 52 acres of walking trails, while still in the heart of town. Ideal for nature-seekers and business travelers alike. Calm, quiet environs in which to read a book— or write one. One loft bedroom with one full bed + one (30" x 70") daybed. One pull-out loveseat in sitting room; 2 stored iBeds. Note all bedding details under Space. Re: pets: one dog allowed. No cats.

Guest favorite

An open living space features a comfortable couch with yellow accent pillows and a coffee table. A fully equipped kitchen is visible, with stainless steel appliances and modern cabinetry. A full-size bed is showcased against a wooden accent wall, with soft bedding inviting restful sleep.

Place to stay in Cross Lanes

4.97 out of 5 average rating, 203 reviews

Spectacular Storage Unit! 😉 Just Off I-64

Have you ever wondered what it would be like to stay overnight in a mini-storage? Probably not, lol! But if you've ever watched HGTV, you'll see that people across the country are creating short-term rentals out of all kinds of crazy things, from shipping containers and barns, to old warehouses. Well, in Cross Lanes WV, we took our cues from those folks on TV and created a short-term rental out of a storage unit! Conveniently located, just off I64, and only 1 mile to the Mardi Gras Casino.

Guest favorite

A cozy living area features a patterned area rug beneath a low coffee table. A plaid couch and a vintage armchair provide seating, while natural light filters through the nearby windows, enhancing the warm atmosphere of the space.

Apartment in Saint Albans City

4.8 out of 5 average rating, 275 reviews

Wisteria Way - 2 Bedroom Apt w/lots of charm

Lovely, fully furnished 2 bedroom apartment with historic charm. Refinished hardwood floors and tons of natural light make this space beautiful and welcoming. Located the in the heart of small town Saint Albans, you’re just blocks away from dining options, library, coffee shop, and parks. Flat sidewalks make the neighborhood perfect for walking or running. Continental breakfast items provided for guests. Hot breakfast offered on weekends (Saturday and Sunday) upon request with 24 hour notice.

Guest favorite

The exterior of a guesthouse is framed by vibrant autumn foliage. A two-car garage is present, with a staircase leading to the entrance. A black bear-themed decoration sits in front, adding a charming touch to the natural surroundings illuminated by warm sunset light.

Guesthouse in Charleston

4.94 out of 5 average rating, 292 reviews

The Bear BnB - Pet friendly, 5 mins to downtown

Take it easy at this almost heaven hideaway. This adorable, Bear themed loft gives you the country setting you’re looking for and the convenience you need. Located just 5 minutes from downtown Charleston and just 3 minutes from Yeager Airport. Enjoy the peace and quiet of nature or hop downtown for an array of shopping and eatery selections. Tour the West Virginia State Capitol topped with its gorgeous gold dome or dive into WVs many adventures. Business or pleasure, you’ll love the Bear BNB.

Guest favorite

A rustic cabin exterior is framed by trees, featuring a wooden porch with steps leading to a front door. Firewood is stacked neatly beside the entrance, while the surrounding area showcases a grassy patch and natural ground cover.

Cabin in Clendenin

4.92 out of 5 average rating, 108 reviews

RealTree Camo Cabin 3

This cabin is rustic and small but super cozy! It's comfortable with a queen size bed, a wood burning stove, air conditioning, fridge freezer, coffee, creamer & sugar provided, a smart tv & more. The creek runs in front of it and is literally up against a mountain, surround by mountains. This cabin is located right beside the shower house. There are beautiful hiking trails, a coal mine is a short hike away and a secret wilderness chapel. Enjoy some simple time up & away from town life.

Guest favorite

A serene pond is surrounded by lush landscaping and illuminated with twinkling lights. The soothing water features a gentle fountain in the center. An old car rests on the shore, adding a unique vintage touch to the peaceful outdoor atmosphere.

Guest suite in Charleston

4.92 out of 5 average rating, 126 reviews

Retreat in the mountains with new hot tub & deck.

Located in Charleston,WV near CAMC Memorial Hospital. 10 minutes away from Yeagar Airport.This fully furnished basement has recently been remodeled which provides a quiet and clean space to relax or work. King size bed and queen size pull out sofa. Air mattresses available. Two full baths. Brand new hot tub. Jacuzzi tub. You can relax and unwind on the deck while over looking the pond and waterfall. At night you can take a leisurely walk around the pond under the lights.Free Wi-Fi.

Top guest favorite

A modern front door is opened wide, inviting guests into the home. A welcome mat featuring the phrase 'WELCOME HOME' is visible on the doorstep. Light-colored flooring can be seen inside, along with a glimpse of decor and furnishings.

Home in Charleston

5 out of 5 average rating, 122 reviews

The 505 on Margaret

Welcome to our custom-built brand-new house in the heart of Charleston West Virginia. This house was completed June 2024 and has been furnished, stocked, and designed with the most modern and updated materials. We have specifically designed this house for nightly, weekly or month-long stays. Located 2 blocks from the Charleston Coliseum and a short walk to the lively capitol street. Check out our other house next door to this one, The 314 on Joseph. Children and pets are welcome.

Guest favorite

The kitchen features white cabinetry and appliances, including a refrigerator, stove, and oven. A small round table with two metal chairs is positioned near a window, dressed in light curtains. A decorative bowl of fruit adds a pop of color on the table.

Apartment in Kanawha City

4.96 out of 5 average rating, 143 reviews

Enjoy our Cozy Garage Apartment

You will love staying in this one bedroom garage apartment, located in the neighborhood of Kanawha City, in the south east section of Charleston , West Virginia. Situated on the Kanawha River, we are minutes from grocery stores and restaurants. We are less than 10 miles from downtown Charleston which has a lot to offer in cultural experiences and locally owned restaurants and businesses. Enjoy the neighborhood feel and enjoy the view of the mountains and the beautiful river.

Guest favorite

A serene river view is captured, featuring the tranquil water flowing beside a grassy area. Lush green trees line the bank, complemented by a mountainous backdrop, creating a peaceful natural setting.

Home in Belle

4.92 out of 5 average rating, 155 reviews

River Retreat,LLC/4.5 m to Charleston/River access

Unwind in the serenity of this beautiful home, situated in the heart of the Appalachian Mountains, where you can gaze at the breathtaking Kanawha River and mountainous backdrop from the comfort of a covered patio. Includes access to the river for fishing or kayaking (gear not included). Minutes away from historic Charleston, offering a balance of access to city attractions with a scenic place to rest after adventuring. Close to Interstates 64, 77, and 79. No cleaning fee.

Guest favorite

The open-concept kitchen features modern appliances and a central dining island with seating for four. Light floods in through large windows, highlighting the sleek cabinetry and tasteful décor. A cozy lounge area is partially visible, adding to the comfortable atmosphere.

Condo in Charleston

4.93 out of 5 average rating, 171 reviews

Cozy Family Apt In Downtown Charleston, WV

Conveniently located near a TESLA CHARGING STATION! This newly remodeled condo style apartment is conveniently located in the heart of downtown. The location is in walking distance to some of the best restaurants, shopping, and more. Just steps away from the Clay Center and CAMC General Hospital for nurses. Staying here you definitely get to experience what it’s like to live downtown and see what all beautiful Downtown Charleston has to offer!

Top guest favorite

A modern living area features a gray sectional sofa adorned with yellow decorative pillows. A white coffee table is positioned in front, and a built-in shelving unit displays colorful decor items. A dining area is visible in the background, showcasing a round table and chairs.

Condo in Charleston

5 out of 5 average rating, 190 reviews

Trier Loft at Renaissance Tower

Trier Loft is a luxury downtown condominium located on picturesque Capital Street in Charleston, WEST VIRGINIA. It is in a 100+ year old building that was originally the KB&T Building. There are spectacular views of Charleston and its surrounding hills from its 5th floor vantage point. It is within easy walking distance to Charleston's most popular restaurants, bars, theaters, specialty shops, and concert venues.

Top guest favorite

A studio apartment features a queen-size bed with a vivid orange comforter, complemented by two orange chairs and a writing desk. Natural light enters through two windows adorned with red curtains, and a decorative area rug enhances the space's warmth.

Apartment in South Charleston

4.98 out of 5 average rating, 119 reviews

An All-Access Bookstore Vacation

Ever thought of having your own bookstore? Here's your chance to live that dream! Plot Twist Books is a charming independent bookshop just minutes from West Virginia's capital city. With our attached studio apartment, you can explore the bookshop 24/7 while learning a bit about the bookselling business. This rental is designed for people who want to go “behind the shelves” at a true independent bookstore.